Triethylamine → 2-Cyano-3-fluoropyridine

HRID 887638

반응식

HRID 887638 반응식
[F:1][C:2]1[CH:3]=[N+:4]([O-])[CH:5]=[CH:6][CH:7]=1.C[Si]([C:13]#[N:14])(C)C.C(N(CC)CC)C>CC#N>[F:1][C:2]1[C:3]([C:13]#[N:14])=[N:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 123084Pyridine, 3-fluoro-, 1-oxide

생성물 1

HCID 70604082-Cyano-3-fluoropyridine

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

The mixture of 3-fluoro-pyridine 1-oxide (0.99 g, 8.75 mmol), trimethylsilyl cyanide (4.80 ml, 35.0 mmol), and triethyl amine (1.84 ml, 13.2 mmol) in 100 ml of CH3CN was heated at reflux overnight. The solvents were removed, under reduced pressure and the residue was partitioned between EtOAc and saturated NaHCO3. The organic portion was separated, dried with Na2SO4, filtered, condensed, the crude compound as purified by flash column chromatography (10 to 20% of EtOAc in hexanes). The titled compound was obtained as a light yellowish solid. MS (ES+): 123.1 (M+H)+. Calc'd for C6H3FN2—122.10.

후처리

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customThe solvents were removed, under reduced pressure
  4. customthe residue was partitioned between EtOAc and saturated NaHCO3
  5. customThe organic portion was separated
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. customcondensed
  9. customthe crude compound as purified by flash column chromatography (10 to 20% of EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-e568494b6bbb429ab93068d83e27aa88
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247430B2

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